Why You Need to Invest in Employees Who Leave Your Organization with James Sinclair | Live with Bottleneck

On this episode of Live with Bottleneck, our guest James Sinclairtalks about why you need to invest in employees who leave your organization. As learning why they left can help you retain, and even hire new great talents for your business.

James Sinclair is the Chief Executive & Co-Founder of EnterpriseAlumni, the market leading Alumni and Retiree Engagement Platform. Outside of his day job, he contributes to media on the future of work, large enterprise innovation, and entrepreneurship.

So if you want to find out how investing goodwill to everyone, even those who are on the way out is good for your company, stay tuned to this episode.

Who is James Sinclair?

James introduces himself briefly, then talks about their company, EnterpriseAlumni.

The concept behind their company is that when someone leaves an organization, it’s often muted and just short goodbyes. James explains that rather than just letting it be the end of the road, you can use this time to find new recruits to referrals. It might seem strange at first, but if you think about it – this employee will most likely have a network of like-minded people with similar expertise. So why not make use of this resource?

“When you join a company everyone high fives, we’re so excited to have you. But when you leave, why does it need to be a weirdly awful, awkward experience? Leaving is inevitable, it’s not a bad thing” – James Sinclair

Leaving is Inevitable

Jaime talks about his past experience in a staffing company, which has soured his perception of said company after he left. It wasn’t so much the fact that he had lost his job, but rather the way it was handled in the end.

James agrees that the way firing or letting go of someone will often affect how an ex-employee looks back in a company.

“How you leave doesn’t represent how you feel. You can hate your job and leave because of that, or love your job but have to leave for other pressing matters. If it wasn’t such an awful experience you might still like the company. Look, you might not have liked the reason they terminated, you might not have liked the financial distress they put on you. But you can still say as a whole, as a company, they were a good company. – James Sinclair

Looking a It from a Different Perspective

James talks about what one of their clients said that stuck with them:

“When someone leaves us, we take credit. You’re going to that job because someone felt we were a great place to teach you, to train you, to get you started for your next role. So you’re leaving because of us not in spite of us so if anything send us the gift box.” – James Sinclair

While it may seem like an overly-positive take on things, it’s actually a common enough reason why people leave. That is, to search for greener pastures, to take their talents and aim higher.

Given the current job climate nowadays, where it is uncommon for people to stay with a company for a decade or so, it’s best to adjust and find ways to grab new promising talents in this ever-shifting job market.

To hear more from James Sinclair and why you need to invest in your employees as they go in and out of your company, continue listening to this episode.


James Sinclair is the Chief Executive & Co-Founder of EnterpriseAlumni, the market leading Alumni and Retiree Engagement Platform. Their software powers the corporate alumni networks of the world’s largest companies, leveraging this vast untapped pool of people for talent, sales, marketing and community. He has a background in large enterprise innovation, having worked for companies including IBM, SAP & EDS. Outside of his day job, he contributes to media on the future of work, large enterprise innovation, and entrepreneurship.

Connect with James Sinclair!

LinkedIn | EnterpriseAlumni

Want more Live with Bottleneck? Visit our website or go to our YouTube channel for more Live with Bottleneck episodes!

Jaime Jay

About Jaime Jay

Meet Jaime Jay – a man who wears many hats, and wears them all admirably. He's a master connector, an entrepreneur extraordinaire, and a published author who knows how to get things done.

Before he found his way to the business world, Jaime served his country as a brave paratrooper in the U.S. Army. But that's just the beginning of his many accomplishments.

He's the founder of the renowned Bottleneck Distant Assistant Services firm, and his book "Quit Repeating Yourself" has become a must-read for entrepreneurs everywhere.

When he's not busy building his empire, you can find him on his beloved Harley Davidson, cruising through the countryside and taking in the invigorating effects of Uitwaaien – a Dutch practice that involves facing the wind to boost health and relieve stress.

He enjoys spending his free time outside building stuff with his wife, Nikita the dog and their two kittens (for now at least) Tommy and Tater.

He is ‘over-the-moon’ happily married to his wonderful wife Sara, his amazing daughter, Jessica, who is serving our country as a United States Army soldier. Jaime and Sara are the proud grand parents of two beautiful little girls.


Get Your Book Now!

Quit Repeating Yourself provides guidance for entrepreneurs, business leaders, and managers to help prevent unknown challenges from ruining their business.

Subscribe to our Newsletter

Related Blogs

Collaborate with Virtual Assistants

Collaborate with Virtual Assistants

Virtual Assistants as the Backbone of Business Success

Supporting Your Vision: Virtual Assistants as the Backbone of Business Success


Focus on Your Core Business: Free up Your Time for Important Business Activities by Hiring Bottleneck Distant Assistants!


Custom-Tailored Assistance: Elevating Your Business with Bottleneck Distant Assistants


Stay Organized, Stay Ahead: Get Organized with Virtual Assistants and Stay Ahead of the Game!


Maximize Efficiency: Streamline Your Operations with Virtual Assistant Support!

Take Control of Your Time: Book a Consultation